


A Halloween to remember.

by SorenMarie



Category: Supernatural
Genre: F/F, F/M, Halloween, M/M, Sexual Situations, chatroom fic, former Destiel
Language: English
Status: Completed
Published: 2018-11-19
Updated: 2018-11-19
Packaged: 2019-08-26 03:10:18
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,629
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16673584
Author URL: https://archiveofourown.org/users/SorenMarie/pseuds/SorenMarie
Summary: You are forced by your roommate to invite people to a Halloween party she’s throwing.  When the two people you like show up together, your roommate comes up with an idea - bring a date and make them jealous.  Is this going to work?





	A Halloween to remember.

**Author's Note:**

> Square Filled: fake dating (SPN Kink Bingo)

****

_Y/N created the room Halloween Party **  
**_

_Y/N added Dean, Charlie, and Sam to the chat._

_Y/N - Roommate and her boyfriend are throwing a Halloween party and told me I had to invite people._

_Dean - I don’t know sweetheart.._

_Charlie - Really guys - where’s your Halloween spirit?_

_Dean - In the bottom of a bottle…_

_Sam - Dean please._

_Y/N -  …_

_Y/N - Please guys.  I don’t want to have the talk with Cas again about how my people skills are rusty.  You don’t have to stay the whole time._

_Charlie - Costumes?_

_Y/N - Of course ;) I’m kind of stoked for mine._

_Sam - Dean, let’s go costume shopping.  See ya later Y/N._

_Dean - See ya at the party sweetheart._

_Sam and Dean have left the chat._

_Charlie - Any hints on what you’re going as?_

_Y/N - Nope.  You’ll have to find out the night of the party._

_Charlie - Time to go pull together an amazing costume._

_Charlie has left the chat._

_Y/N - I can’t wait to see what they put together._

_Y/N has left the chat._

_**_

_Meg has entered the chat._

_Cas has entered the chat._

_Cas - I see Y/N has taken my advice and invited some people to our party._

_Meg - Could our dear Y/N be any more obvious?_

_Cas - ?_

_Meg – She obviously wants to bang the elder Winchester and Peppy Longstockings like drums but she’s too scared._

_Cas - By elder Winchester, you do mean Dean right? Granted John Winchester is a handsome man.._

_Meg - Okay, tone it down there Wings._

_**_

_Dean, Charlie and Sam have entered the chat._

_Charlie - I don’t know how we did this without coordination._

_Dean - I’m just as surprised as you are._

_Charlie - What did Sam come as again?_

_Dean - He’s a star wars rebel alliance fighter pilot.  At least he picked out a costume._

_Sam -  Hey Dean?_

_Dean - Yeah Sammy?_

_Sam - Bite me._

_Charlie - Do I have to separate you two?_

_Cas has entered the chat._

_Cas - Hello Dean.  Hello Sam.  Hello Charlie._

_Charlie - Hello robot Cas._

_Dean - Charlie, don’t be rude.  Cas isn’t a robot._

_Sam - He was more robot like when we first met him.  You probably could’ve given him the Turing test…_

_Cas - Still not a robot though._

_Dean - Ain’t that the truth ;)_

_Sam - Dean, please._

_Charlie - Where’s Y/N?_

_Cas - She’s around, I think._

_**_

_Meg - Your lady love and the big dummy are downstairs asking about you._

_Meg - You have to come out sometime._

_Y/N - I know. Cas sent me a picture of them.  Meg, they came in matching costumes and everything.  There’s no way they didn’t come here together._

_Meg - There is one solution - you could always make the two of them jealous._

_Y/N - It would never work Meg._

_Meg - Never say never ;)_

_Y/N - who would even agree to something like that?_

_Meg has added Crowley to the chat._

_Crowley - Hello darling._

_Y/N - Really Meg? *sigh* Hello Crowley._

_Crowley - Don’t sound so excited to see me.  I have it on good authority that we need to make Squirrel jealous?_

_Y/N - This is going to backfire somehow, I know it.  It’s not just him._

_Crowley - Ah yes the red head as well?_

_Meg - Stop being a negative Nancy.  Crowley, are you actually dressed up like a king?_

_Crowley - It is Halloween after all._

_Meg - Someone thinks highly of himself._

_Y/N - lmao.  I’ll be downstairs in a minute._

_Meg - Good._

_**_

_Dean - I’ve seen Cas’s costume somewhere before._

_Charlie - You know where it’ll never end up?_

_Dean - … where_

_Charlie - On your floor again, because Cas has moved on - you should too._

_Sam -  Damn Charlie, look at you taking my job._

_Charlie - You hush._

_Dean - Is he dressed up as the pizza man?_

_Charlie - Does that make Meg the babysitter?_

_Sam - The both of you need to stop confusing porn with real life._

_Sam - So I have yet to see Y/N…_

_Cas - She’s hiding out in the study with Crowley.  Apparently he’s her date for the night._

_Charlie - Why, he’s old enough to be her father._

_Sam - Maybe she likes that._

_Dean - There’s no way.  Also Sam, it’s not right to kink shame someone._

_Sam - You would know all about that wouldn’t you - or have you found someone will wear a Zorro mask and slap you during sex?_

_Dean - Shut it bitch._

_Sam - Jerk._

_Charlie - As if you’re all pure and innocent Sam…_

_Dean - Oh hey Sam, look Eileen’s here._

_Sam -  I’ll be back later._

_Sam has left the chat._

_Charlie - His crush on her is so adorable._

_Dean - It is._

_Meg has entered the chat._

_Meg - I swear the three of you are going to be the death of me._

_Charlie - What’d we do?_

_Meg - The matching costumes Peppy._

_Dean - ?_

_Charlie - Dean’s dressed as Jon Snow, and I’m Daenerys.._

_Meg - That’s my point!  Y/N is looking super hot as Khal Drogo and yet she hasn’t talked to the two of you all night._

_Dean - We talking regular Khal Drogo?_

_Meg - Female Khal Drogo, Dean bean._

_Dean - don’t call me that._

_Charlie - I’m going to go say hi, be right back._

_Charlie has left the chat._

_Charlie has entered the chat._

_Dean - That was fast… so did you find her._

_Charlie - I can’t handle this right now.  I’m in love._

_Meg - So that’s what it takes to get.your attention._

_Charlie - I will find you and slap you._

_Dean - On a scale of 1 to 10…what are we looking at?_

_Charlie - 100._

_Dean - Really?_

_Charlie - Go find her if you don’t believe me._

_Dean has left the chat._

_Dean has entered the chat._

_Dean - Holy shit you were right.  Why is Crowley her date?_

_Charlie - You know how the song goes right?  He does look amazing in that suit._

_Meg - Ew.  That’s my boss you’re complementing._

_Charlie - and?_

_Meg - I need to find Castiel, and step away from all of this._

_Meg has left the chat._

_Charlie - Dibs!_

_Dean - Dibs!_

_Charlie - Really Dean?_

_Dean - Don’t yell at me when you did the exact same thing._

_Charlie -  Wanna make a bet?_

_Sam has entered the chat._

_Sam - This won’t end well._

_Dean - Shut it Sam.  What’s the terms?_

_Charlie - Winner gets to go on a date with Y/N._

_Dean - and the loser?_

_Charlie -  I didn’t think that far._

_Dean - Loser has to clean the bunker for a month._

_Charlie - Oh it’s on Winchester.  Apple bobbing first?_

_Dean - Okay sure._

_Sam - Party games are not the way to go but what do I know -sigh-_

_Dean and Charlie have left the chat._

**

You heard the doorbell ring and with a sigh, you made your way downstairs.  You smiled a little when you opened the door and Crowley was standing on the other side.  You chuckled at his costume - which was his normal black suit with a crown upon his head.  “I love your costume Crowley.”

“Why thank you darling.”  He gently kissed your knuckle as the two of you made your way inside.  You stopped by the kitchen as Crowley picked up a drink, he offered to get you one of your own, but you declined.  Hand in hand, you made your way to the loveseat in the living room.  It was the only place where it was remotely quiet.

“How are you doing, kitten?  You can be honest with me, I won’t judge.”  You watched as he took a sip of his drink.  There were a few thoughts running around your head and you considering lying, but what was the point?  

“I’ve been better.”

“It’s rough having feelings for more than one person.  I know this might come off as forward but I could make you forget about them.”  You gasped as Crowley picked you up and settled you into his lap.  You couldn’t help it as hid your face in your hands.  Crowley laughed as you moved your arms around his waist.  

“How so?”  Your eyes met for a brief second.  “Wait…do I really want you to answer that?”

“I think deep down part of you is curious and that’s why you asked.”

“How would you do it then?”  

“A gentleman would never talk to a lady like that.”  He watched your face for a split second before he continued.  “However, I can see those gears turning.  It would be tender at first - I would make sure every need you have is met.  Has anyone ever gone down on you?”

Your felt your face flush.  “Once, and he was horrible at it.”

“I would never leave you unsatisfied.  In fact - we wouldn’t leave the bedroom all night.”  

Feeling a little bold, you leaned into him.  “What about you?”  

“No, this would be all about you.”  He smirked as he felt you squirm in his lap.  “I can tell this is getting you bothered Y/N, do you want to sneak away and take care of your little problem or would you like some help?”

“I’m fine, please continue.”  You had to bite the inside of your cheek to keep the moans from coming out.  

“I would make sure you’re ready for me then and only then would I enter you.”  Your face was red as Crowley kept whispering the things he would do to you in your ear.  Cas and Meg watched the two of you from doorway and looked at each other.  Meg knew she had to do something - otherwise you’d go home with Crowley.    

_Meg - Hey guys - if you’re going to have sex, could you not do it in the living room?_

_Y/N - Ohmygod Meg, why would you even…_

_Crowley - and I thought my mother was a cock block._

_Meg - We could hear her moaning in the kitchen.. It got their attention however._

_Y/N - What?_

_Crowley - It worked?_

_Meg - It stopped their stupid competition.._

_Y/N - What competition, Meg?  You know what - I’ll go ask about it myself._

**

_Y/N - Can anyone tell me why Dean and Charlie are being super competitive all of a sudden?_

_Sam - I can’t. Sorry._

_Y/N has left the chat_

_Sam - Damn it, you two._

_Dean - What?_

_Charlie - I just watched Y/N storm upstairs, what did we do wrong?_

_Sam - Well…_

_Cas has entered the chat._

_Cas - Y/N is in distress.  What happened?_

_Dean - We made a stupid bet and she caught the tail end of it._

_Sam - Told you it would blow up in your face._

_Charlie - I was winning too._

_Dean - We were tied at best._

_Charlie - …_

_Dean - Truce?_

_Charlie - Fine._

_Cas - I don’t understand why you were fighting…_

_Sam - How do I explain this? Both my brother and Charlie like Y/N._

_Cas - Why would you fight over something like that? It’s kind of obvious she likes the both of them._

_Dean - What?_

_Charlie - Cas what do you mean?_

_Cas - I’m afraid I’ve said too much._

_Cas has left the chat._

_Sam - I think your best bet right now is to go talk to Y/N.  I know you don’t like this Dean, but tell her how you feel.  Charlie - you too. Then maybe this will stop you from acting like idjits in the future._

_Sam has left the chat_

Charlie was the first one to knock on your bedroom door.  She heard noises and when she cracked the door open, you were half way out the window.  “Y/N, where are you going?”  You sighed and pointed to the door leading to the balcony.  Whenever you needed to think, this is where you would always go.  

“I just needed to think about something.”  She took a seat next to you and when you heard Dean tap on your bedroom door, Charlie yelled at him.  

“Hi.”  

“Hi Dean.”  

He pulled an empty chair next to the two of you and you smiled briefly.  “Can either of you explain what the hell was going on?”

You watched Dean rub the back of his neck and Charlie couldn’t meet your eye.  “It’s dumb really.”

“Tell me.”  You grabbed a hold of Dean’s hand forcing him to look at you.  “Please?”

He cleared his throat and you felt him lace his fingers with your hand.  “We had a bet that who won the most party games would get to ask you on a date.”

“Wait, why would you do that if you two are going out?”

“What?”

“You honestly think that Dean and me are dating?”  Charlie practically screeched and you heard Meg yell from downstairs to keep it down.  

“What else would I think when you came to the party in matching costumes.  I thought only couples did that.”

“Oh sweetie.”  Charlie placed her arm over your shoulder and pulled you in closer.  “I can appreciate how attractive Dean is but he’ll never be my type.”  

“What on earth do you mean?”  Dean chuckled and moved his chair closer towards the two of you.  

“Dean’s one of my best friends, hell he’s the closest thing I have to a brother but I’m not attracted to him.  At all.”

“You like girls, of course…”  She watched as you processed that information.  “And you like me?”

“Of course, why else would I fight this knucklehead all night to go on a date with you.”  She felt you kiss her on her cheek and Charlie smiled.

“What about you sweetheart, is there anything you want to tell us?”  Dean watched as you bit your lower lip and tried to avoid looking  into his eyes.  

“I don’t see why the two of you had to compete at all - if you would’ve asked me, I would’ve said yes.”

“Wait, what are you saying right now Y/N?”  Dean watched as you shifted towards him.

“I can’t believe I’m telling you like this.  I like the both of you.”

“As friends right?”  

_Y/N - I swear to Chuck, Dean you are so dense._

_Charlie - Lmao we are in the same room, I don’t think he’s going to check this just yet.  But oh my god Y/N - get it girl.  Wait…_

Charlie grinned as she watched you pull Dean closer and kiss him.  Friends didn’t kiss the way you were kissing him.  Maybe this would work out after all.

_Dean - Okay okay, I get it sweetheart._

_Charlie - shebahhdgdg_

_Dean - Charlie?_

_Y/N - she’s a little busy at the moment Dean…_

Dean chuckled as he watched Charlie’s phone fall onto the couch.  “Should I leave the two of you alone?”

“No way, we’re not done with our conversation.”

“I would never ask you to choose between the two of us.”

“I like both of you and I want to be with both of you.”  A small moan slipped out when Charlie hit a sensitive spot on your neck and Dean raised an eyebrow.

“We can talk about this later, Y/N.  Let’s go back to my place..”  Charlie grinned and Dean winked at you.

_Y/N - Dean, if this escalates, you have my permission to watch._

_Dean - I can do more than watch sweetheart._

_Y/N - Meg is going to kill me._

_Dean - At least we know now…_

_Y/N - You’re lucky Meg told me what was going on…_

_Dean - Oh?_

_Y/N - Yeah, I might’ve slept with Crowley if she didn’t say anything._

“Please tell me you’re joking, Y/N.”

_Meg - Guys, if you’re going to have sex, please go somewhere else.  Y/N, I love you but I don’t need to hear Dean’s sex noises again._

_Dean - We’ll be out of your hair shortly.  Y/N is packing an overnight bag._

_Dean has left the chat,_

_Charlie has left the chat._

_Y/N - So do I give you details tomorrow or no?_

_Meg - Of course.  Be safe and use protection.  Also don’t do anything I wouldn’t do ;)_

_Y/N has left the chat._

_Meg has left the chat._


End file.
